Aldehydes and ketones (A-level only)

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Question 8
Medium

Butanone reacts with potassium cyanide, followed by dilute acid, to form 2-hydroxy-2-methylbutanenitrile.

1.

Name the mechanism for the reaction between potassium cyanide and butanone.

[1]
2.

The 2-hydroxy-2-methylbutanenitrile formed by the reaction is a mixture of equal amounts of two isomers.

  • State the name of this type of mixture.
  • Explain how the structure of butanone leads to the formation of equal amounts of these two isomers.
  • Draw 3D representations of the two isomers of 2-hydroxy-2-methylbutanenitrile to show the relationship between them.
[5]
3.

2-Hydroxy-2-methylbutanenitrile can be used in the synthesis of the monomer, 2-methylbut-2-enenitrile, CH3C(CN)=CHCH3\text{CH}_3\text{C}(\text{CN})=\text{CHCH}_3CH3​C(CN)=CHCH3​. Suggest a suitable reagent and conditions for this dehydration reaction.

[2]
4.

Draw a section of the addition polymer poly(2-methylbut-2-enenitrile), showing three repeating units.

[2]

Aldehydes and ketones (A-level only) Questions

  1. A Level
  2. /Chemistry
  3. /Aldehydes and ketones (A-level only)